


Study Session

by Taciturn



Series: Obey Me! Shenanigans [8]
Category: Shall We Date?: Obey Me!
Genre: Bondage, Breeding Kink, Demon Sex, Double Penetration, F/M, Gags, Multiple Orgasms, Overstimulation, Size Kink, Slight degredation, Tail Fucking, Unedited bc yolo
Language: English
Status: Completed
Published: 2021-02-20
Updated: 2021-02-20
Packaged: 2021-03-16 04:02:36
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,616
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29570031
Author URL: https://archiveofourown.org/users/Taciturn/pseuds/Taciturn
Summary: Barbatos’ teaching methods are unorthodox, but effective
Relationships: Barbatos (Shall We Date?: Obey Me!)/Reader, Diavolo (Shall We Date?: Obey Me!)/Reader
Series: Obey Me! Shenanigans [8]
Series URL: https://archiveofourown.org/series/1837717
Comments: 7
Kudos: 167





	Study Session

**Author's Note:**

> I wanted to write Barbatos tail fucking in great detail. So I did it. Please enjoy.

As a demon in control of time itself, it wasn’t a surprise that Barbatos excelled in history. When he offered to give you extracurricular lessons in his free time to help you float your grade in Demonic History, you were more than eager to jump on the chance to spend more time with him and get some much needed help with a subject you struggled in. You expected him to be strict. With the way he regularly carried himself, you knew that he wouldn’t go easy on you.   
  
What you _didn’t_ expect was to be face down, ass up on a couch in a parlor. Your arms flush against your side as your wrists were tied to your bent knees. A spreader bar kept your legs apart and your pussy easily accessible during his lesson. He expected you to be in that position for hours considering how much you had to go through and at least had the foresight to wedge a cushion under you to help you hold the pose he put you in. Your underwear had been pushed to the side at the beginning, but after it slipped back over your holes, Barbatos made the executive decision to just rip them off for the remainder of his lecture.   
  
He had gagged you. Something about “We must make sure we do not disturb Lord Diavolo while he is working.You can save any questions you have for the end of the lesson”   
  
You were a drooling mess with your mouth stretched open over the gag, your muffled moans interspersed with labored, deep breathing through your nose.   
  
The butler sat in front of you, his crotch in full view so you could see how much he was enjoying his private lecture with you. You noticed his long tail snake around you, caressing your back and flipping over your skirt so he had full access to your holes and your ass. All the while, he continued to nonchalantly read from the book in his hand. The cool air hitting your heated core only made your focus blurry and his words faded away as you tried to hide your arousal.   
  
You were fading away into a land of fantasy until you felt something gently stroke your sopping folds. The tip of his split tail trailed up and down your pussy, coating itself in your essence. You looked up at him expectantly, hoping he would continue but he only glanced down at you for a brief moment before continuing onto the next paragraph. His tail stopped its ministrations and he waited for you to catch your breath.   
  
“ _Good_ students get rewarded for paying attention.” He explained coolly when you let out a needy whine, struggling against your restraints and pressing yourself closer to the teasing tip of his tail.   
  
He smirked and only waited for you to get the hint. Not moving nor giving you any of the pleasure you craved until you behaved as he saw fit. Only then did he continue to play with your pussy. The twin tips of his tail spread your lips apart as he educated you on the long history of Demonic royalty. Your hot hole ached to be filled, yet he only ever teased at its entrance. He knew what you wanted and he wasn’t about to give it to you until you proved to him you were a _good student.  
_  
His lecture dragged on, but you desperately hung onto every word, committing them to memory in his sultry voice if only for a chance to be satisfied. His tail eventually slipped into you and the lewd moan that came from the back of your throat was louder than you anticipated.   
  
Barbatos chuckled, pushing one split end into you while the other circled your clit. You whined, breathing heavily through your nose as his words once again faded into the back of your mind while you were awash with pleasure. Thin as the tips were, they were dexterous and the tip that was within you squirmed inside of you, pressing and and exploring all your sensitive spots. The tip on the outside focused on your swollen clit, giving it all the attention you could wish for, pushing back the fleshy hood and stimulating the sensitive bundle of nerves directly.   
  
“Are you ready for the next lesson? The timeline of Demon... conquests is a long one and I do hope you won’t be falling asleep.”   
  
You whined, nodding vigorously and you were rewarded with the feeling of his tail pushing further into you. Your eyes rolled back and you moaned. You weren’t filled yet, not nearly satisfied with the teasing he was giving you. But perhaps, if you were able to pay attention for the rest of his lessons, he would give you more.   
  
Your poor, sensitive clit was being worked into a state of over stimulation. The tip of his tail rubbed it in all the best ways. He had barely begun the next lecture before you let out a muffled scream, clenching around the thin appendage inside of you while he continued to relentlessly rub your clit. Your ears rang, from the force of your orgasm, but Barbatos didn’t seem to pay you any mind, easily reading from his book and slowly thrusting his tail in and out of you while you struggled to focus.   
  
He no longer sat in front of you. The last time you looked, you could see a growing bulge in his pants and you were grateful to know he was somewhat affected by all of this as well. He stood behind you now, getting a full view of your ass and your dripping hole. Your swollen pussy and clit was a lovely, enticing sight and he gently ran his hand up and down your soaked thighs, trailing it up to cup your ass before giving it a firm slap.   
  
“Pay attention. I shouldn’t have to tell you this twice.”   
  
You let out a pathetic whimper, wishing you could at least beg for him to fuck you. But the gag in your mouth prevented you from expressing your deepest desires.   
  
“No wonder you’re failing. Look at you.” He sneered, slapping your ass once more. The tip that was caressing your clit now joined the one inside of you. The twin tips squirmed and writhed in your tight walls, pressing up against the sensitive channel and you shuddered as they pushed deeper and deeper inside of you, exploring every nook and cranny of your most sacred hole. “You’re so easily distracted. How disappointing.”   
  
The lesson had been put aside for the time being. He was much more focused on your punishment now for being unable to pay attention. The tips of his tail retreated to your entrance once again, this time scissoring you open, exposing you the demon behind you. “How disgusting... you’re so turned on by my _tail_.” He cooed, the slightest hint of malice in his voice. Somewhere in the interim, he had removed his gloves and now his soft hands traced slick trails of essence that flowed down your thighs before he pushed two fingers into your open hole.   
  
Your cunt eagerly accepted the digits, clenching around them while his tail continued to keep the entrance stretched wide for him. The wet sounds of his fingers thrusting in and out of you filled the room for a few minutes before he casually went back to discussing Demonic history as if he wasn’t finger fucking you to oblivion at that moment.   
  
You remembered cumming around his fingers around the time he told you about Lord Diavolo taking reign over the Devildom. Whatever names that came before that were a blur as you reeled in the sensation of our climax. His tail at last left your abused pussy alone as his fingers withdrew from you. You could hear Barbatos taking a moment to lewdly lick his fingers clean while he took a pause in between his lesson to let you soak in his teachings.   
  
That didn’t last very long though as he started speaking about his Lord’s early years on the throne. His tail once again entered you. This time, the tapered tip reached further inside of you than before. This time, it was a test to see how much of him you were willing to take. This time, you were gasping behind your gag, struggling for breath as he inched himself further and further inside of you. The writhing tips of his tail pushing aside your walls to make room for him until they stopped at your cervix.   
  
Tears started to roll down your eyes as you tried to comprehend Diavolo’s early achievements all the while the tip of his tail probed at your deepest spot and your entrance was stretched painfully wide open. He toyed at the tightly closed entrance within you, briefly teasing it before he started a regular thrusting pace in and out of you. Your pussy eagerly accepted the abuse, loving every inch of his tail that fucked you, its slick, smooth surface glided along your walls and sent you into paradise.   
  
And then, the pace quickened as he excitedly discussed even more of his history of service to Diavolo. The tips of his tail no longer teased at your cervix, they demanded entrance and they forcibly wriggled their way into you, hitting you deeper than before. Your very core was touched as he found himself exploring your womb and the carnal thoughts of filling it up with his seed interrupted his lesson for a bit.   
  
“Which... brings us to up to more present day.” He finally announced once he was satisfied with exploring you with his tail. “I hope you got all of that... I will be testing you later on this.”   
  
You gave him a feeble nod and a quite whine in confirmation. You weren’t sure how much you had actually learned considering how many times your mind had blanked out when you came around his tail.   
  
“Very good. I think it’s time for a well deserved break.”   
  
You heard the rustle of fabric and you heard the tell tale sounds of him releasing his cock from the confines of his pants. Glancing back, you took a look at it in its fully erect glory. His cock looked as if the tips of his tails had twisted together into a tapered spiral. Precum dribbled freely from the tip. His gaze met yours and with one last knowing smile, he plunged into your waiting hole.   
  
You could feel every ridge and bump of his cock as he entered your abused hole without much effort at all. His tail found the tight ring of muscle that held your asshole closed and started to tease there too while he set a brutally quick pace. His hand laced through your hair and pulled your head up to give him better leverage as he pounded into you. He knew just how deeply he had to go in order to fill your womb with his seed.   
  
As composed as he seemed to be on the regular, he wasn’t immune to the base needs of a demon. His dick dragged itself along your sore walls, relishing in how tight you were even after his tail had fucked you so thoroughly. Speaking of which, that appendage, still liberally lubricated with your essence had found its way past your anus and you were soon met with the feeling of being filled in both your holes.   
  
Though the base of his cock wasn’t as thick as his tail, the feeling of being penetrated in both holes had you stretched and full in a way you never experienced before. He worked your body like a toy, his tail and cock thrusting in rhythm that had you seeing stars. Barbatos was a much stricter teacher and a harsher lover than you could ever imagine.   
  
He knew the deepest parts of you and knew how you craved fitting every inch of him inside of you. He knew how hard to thrust to have you wheezing past your gag. He knew _everything_ and you were more than happy to let him use you as he saw fit. The butler’s fingers dug into your hips as he held you in place while he fucked you, angling you so he could go _deeper_ reach you right in the womb and breed your pretty little body until it was full of his seed.   
  
The thought of seeing your hole dripping with his cum was the last thing he needed to be sent over the edge. With a hard thrust from his cock and a harder push from his tail, he buried himself as deep as possible inside of you, releasing his load and flooding your canal with his essence. He groaned, panting in the after wake of his release. The warmth of his seed in you brought your walls down once again and you clenched around him, milking and accepting all he gave you.   
  
Pulling out slowly, he was met with the vision he had imagined. Your pussy gaping wide, dripping with a mixture of your fluids and his cum. His tail also retreated and he was pleasantly surprised at how lovely you looked with _both_ your holes stretched open. He hummed in content, his finger trailing up and down your thighs, admiring the slick mess there.   
  
“Ah, I take it the lesson went well then?”   
  
Diavolo’s voice rang through the room and you felt a thrill of embarrassment and shock run through your spine. You squirmed, trying to close your legs and expose less of yourself to the Demon prince, but a firm slap on your ass caused you to stop. Your face flushed and you buried it the drool soaked cushion below you.   
  
“Very well. I’m sure she’s learned a lot.” Barbatos’ voice was cool and calm. He at last worked the gag off of you and once it was removed, you gasped for air relieved to at last take a deep breath unhindered. “I was just about to test her on what she learned. Would you like to oversee that?”   
  
“Oh, absolutely.” Diavolo’s tone was chipper and eager. You wondered just how much you would be able to recite after a lesson like that and your mind scrambled to recall the lectures Barbatos had given you.   
  
In your frantic recollecting, you had missed the sound of the demon prince’s pants coming undone, and it wasn’t until you felt the hot and heavy weight of his cock on your ass cheek when you realized what was about to happen. “So... start at the very beginning.” He announced, rubbing his cock in the juices that were liberally flowing out of you. Even if you had just cum, even if you were tired and over stimulated, the thought of accepting the _prince_ had you wet and aching for him to fill you up.   
  
A quick glance back and your heart skipped a beat seeing his size and the regal shape of his knot. You gulped and quickly went back to recalling your ‘lessons.’ “What did you learn about our history?” he asked, pushing the thick, bulbous head into your sore pussy. “It’s been a while. I’m sure I could use a refresher.”   
  
You gasped and started babbling. No amount of preparation could have allowed you to be prepared for taking Diavolo, but you were a _good_ student and you were going to show them just how much you learned.   
  
And for every inch of him you took, you remembered yet another fact from Barbatos’ lecture. Surely after this, you would pass your classes with flying colors, though; the thought of failing them more often was rather enticing.


End file.
